Simple reaction conditions for the formation of ketonitrones from ketones and hydroxylamines

J Org Chem. 2009 Nov 6;74(21):8381-3. doi: 10.1021/jo901653d.

Abstract

The condensation of ketones and hydroxylamines to form ketonitrones was reinvestigated by using thermal conditions previously found to minimize hydroxylamine decomposition (t-BuOH, 110 degrees C). This simple approach allows the formation of exocyclic, acyclic, and alpha,beta-unsaturated ketonitrones with benzylic, linear, and branched nitrogen substituents in modest to excellent isolated yields.